EP2482795B1 - Antiperspirant composition - Google Patents

Antiperspirant composition Download PDF

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Publication number
EP2482795B1
EP2482795B1 EP09793162.0A EP09793162A EP2482795B1 EP 2482795 B1 EP2482795 B1 EP 2482795B1 EP 09793162 A EP09793162 A EP 09793162A EP 2482795 B1 EP2482795 B1 EP 2482795B1
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EP
European Patent Office
Prior art keywords
composition
oil
aluminum
weight
fatty acid
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Application number
EP09793162.0A
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German (de)
English (en)
French (fr)
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EP2482795A1 (en
Inventor
Aixing Fan
H. Steven Misner
Latonya Kilpatrick-Liverman
Elizabeth Linn
Darrick Carlone
John P. Hogan
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Colgate Palmolive Co
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Colgate Palmolive Co
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Publication of EP2482795A1 publication Critical patent/EP2482795A1/en
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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00—Anti-perspirants or body deodorants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/361—Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin

Definitions

  • fatty acids can be selected as a gellant in an antiperspirant/deodorant composition. While fatty acids can be used, they are not used in practice because they result in products that create an undesired level of softness, which results in too much payout of the product. It would be desirable to use fatty acids because of the lower cost, but there needs to be a solution to the softness caused by the fatty acids.
  • the present invention provides an antiperspirant composition according to claim 1.
  • ranges are used as a shorthand for describing each and every value that is within the range. Any value within the range can be selected as the terminus of the range. In the event of a conflict in a definition in the present disclosure and that of a cited reference, the present disclosure controls.
  • the present invention includes plant (natural) oils in an antiperspirant composition that overcomes the expectation that the composition will have an oily feel and leave a white residue.
  • the composition includes a fatty acid.
  • the fatty acid is present in its acid form. While fatty acids are present in plant oils, this is an additional amount of fatty acid that is added.
  • the saturated fatty acid is stearic acid and/or palmitic acid. In one embodiment, the saturated fatty acid is C16.
  • the amount of fatty acid in the composition is greater than 7 weight% and may be up to 30 weight% of the composition . In other embodiments, the amount of fatty acid is at least 7.5, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, or 25 weight %. In certain embodiments, the amount of saturated fatty acid is 15 to 21 weight%. In other embodiments, the amount of saturated fatty acid is 16 to 20 weight%.
  • the composition includes a plant oil.
  • plant oil it is meant that the oil is obtained from a plant.
  • plant oil does not include fragrances.
  • the plant oil has a melting point below 40°C or below 35°C or below 30°C.
  • the plant oil is at least one oil chosen from palm kernel oil and coconut oil.
  • the plant oil is a combination of palm kernel oil and coconut oil.
  • the amount of plant oil in the composition is at least 12 weights %. In certain embodiments it may be a up to 20 weight% of the composition. In certain embodiments, the amount is greater than 13, 14, 15, 16, 17, 18, or 19 weight % in the composition. In certain embodiments, the amount of plant oil is greater than the amount of volatile silicone in the composition. In one embodiment, there is no volatile silicone in the composition. In other embodiments, the amount of plant oil is more than 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, or 95 weight % of the combined weight of plant oil and volatile silicone (if present).
  • the combination of a saturated fatty acid (in particular a C16 fatty acid) in an amount of 15-21 weight% (or 16-20 weight%) with a plant oil (palm kernel or coconut oil) in an amount of 12-20 weight% provides a structure with a commercially acceptable compression value, which can be at least 3500 g.
  • additional (second) gellants can optionally be included in the composition.
  • Gellants are those materials known in the art that structure the composition. Examples include, but are not limited to, waxes, fatty alcohol, hydrogenated vegetable oil, a hydrocarbon wax, esters of fatty acid and fatty alcohol, triglycerides, or other cosmetically acceptable materials, which are solid or semi solid at room temperature and provide a consistency suitable for application to the skin.
  • the hydrogenated oil is hydrogenated soybean oil. In one embodiment, the hydrogenated soybean oil is almost, but not fully hydrogenated. The amount of hydrogenation is measured by the iodine value. The iodine value can be measured by ASTM D5554-95 (2006). In one embodiment, the iodine value of the hydrogenated soybean oil used herein is greater than 0 to 20. In one embodiment, the iodine value is 1 to 5. In another embodiment, the soybean oil is fully hydrogenated with an iodine value of 0. In another embodiment, the iodine value is up to 20. Reference is made to United States Patent Publication No. 2008/0187504A1 .
  • the gellant includes a partially hydrogenated soybean oil having an iodine value in the range of about 75 to about 80.
  • This partially hydrogenated soybean oil can be obtained from Cargill under the product designation S-500. Reference is made to United States Patent Publication No. 2008/0187503A1 .
  • This material has a typical fatty acid distribution shown in the table below. Amounts shown are in % by weight. C16:0 10.5-11.2 C18:0 6.8-7.5 C18:1 61-65 C18:2 16-19 C18:3 0-0.2 Saturates 17.5-19.5 Trans 34-39
  • the hydrocarbon wax can be a hydrocarbon of the formula C n H 2n+2 , wherein n is 20-100, and the hydrocarbon is at least 90% linear.
  • the hydrocarbon is a paraffin.
  • the hydrocarbon is polyethylene.
  • An example of a polyethylene can be found in United States Patent No. 6,503,491 .
  • the polyethylene has a weight average molecular weight in of about 300 to about 3000 and a melting point of about 50 to about 129°C.
  • he hydrocarbon is synthetically made from methylene to form a polymethylene.
  • the fatty alcohol can be any fatty alcohol.
  • the fatty alcohol is stearyl alcohol.
  • the gellant includes hydrogenated castor oil (castor wax).
  • the melting point of the castor wax is 70 to 90, or it can be 70, 80, or 90.
  • the gellant is a combination of the hydrogenated soybean oil with a fatty alcohol or the hydrocarbon.
  • the composition includes an antiperspirant active.
  • antiperspirant actives include, but are not limited to, aluminum chlorhydrate, aluminum chloride, aluminum sesquichlorohydrate, aluminum-zirconium hydroxychlorides, complexes or adducts of the above-mentioned active ingredients with glycol, such as propylene glycol (for example, "Rehydrol” II from Reheis Chemical Co.), and combinations thereof.
  • glycol such as propylene glycol (for example, "Rehydrol” II from Reheis Chemical Co.)
  • Known aluminum-zirconium salts in combination with neutral amino acids, such as glycine (e.g., aluminum-zirconium tetrachlorohydrex Gly) can also be used.
  • any of the Category I active antiperspirant ingredients listed in the Food and Drug Administration's Monograph on Antiperspirant Drug Products for overall-the-counter human use (Oct. 10, 1973) can be used.
  • the antiperspirant active is an aluminum salt and/or an aluminum-zirconium salt, such as those described above, that are further stabilized by betaine and a calcium salt. More information about betaine and calcium salt stabilized antiperspirant salts can be found in U.S. Patent Application Publication No. 2006/0204463 to Tang et al.
  • the antiperspirant active such as those described above, is selected to have a low metal to chloride ratio. Examples of these antiperspirant actives can be found in U.S. Patent No. 6,375,937 to Chopra et al. and in U.S. Patent Application Publication No. 2004/0109833 to Tang et al.
  • the type of salt of interest an aluminum zirconium tetrasalt or octasalt free of glycine are used wherein aluminum zirconium salt is stabilized by Betaine and has a metal to chloride ratio of about 0.9:1 to about 1.3:1 (and in other embodiments of about 0.9:1 to about 1.2:1 or about 0.9:1 to about 1.1:1).
  • the Al/Zr atomic ratio can be about 3.2:1 to about 4.1:1.0 and the Betaine:zirconium mole ratio can be about 0.2:1 to about 3.0:1 (or in other embodiments of about 0.4:1 to about 1.5:1).
  • Another salt that can be used is an aluminum chloride salt buffered by Betaine, wherein the salt has a metal to chloride ratio of 0.9:1 to 1.3:1 (and in other embodiments of about 0.9:1 to about 1.2:1 or about 0.9:1 to about 1.1:1).
  • the Al/Zr atomic ratio is about 6.2:1 to about 10.0:1 and the Betaine:Zr mole ratio is about 0.2:1 to about 3.0:1 (or in other embodiments of about 0.4:1 to about 1.5:1).
  • the Betaine is incorporated during the synthesis of the salt so as to maximize the stabilizing effect this ingredient has (especially on the zirconium species).
  • it can be post added to a glycine-free salt along with additional active phase ingredients to form a Betaine stabilized active.
  • Examples of commercially available glycine-free low M:Cl ratio tetrasalts and octasalts include, but are not limited to, REZALTM AZP 955 CPG and REZALTM AZP 885 respectively (both from Reheis Chemical Company, Berkeley Heights, NJ).
  • REZALTM AZP 955 CPG and REZALTM AZP 885 respectively both from Reheis Chemical Company, Berkeley Heights, NJ.
  • a more detailed description of making such commercially available salts can be found for example, in U.S. Patent Nos. 7,074,394 and 6,960,338 . Further examples of making these types of salt complexes are described in U.S. Patent Application Publication No. 2004/0198998 and United States Patent No. 7,105,691 .
  • antiperspirant formulations preserve their fragrance stability upon ageing when the Al/Zr salt is used in association with Betaine.
  • the antiperspirant active can be a calcium salt stabilized antiperspirant active.
  • examples of calcium salt stabilized antiperspirant actives can be found in U.S. Patent Application Publication No. 2006/0204463 .
  • any new ingredient, not listed in the Monograph such as aluminum nitratohydrate and its combination with zirconyl hydroxychlorides and nitrates, or aluminum-stannous chlorohydrates, can be incorporated as an antiperspirant active.
  • Antiperspirant actives can include, but are not limited to, the following: astringent salt of aluminum, astringent salt of zirconium, aluminum bromohydrate, aluminum chlorohydrate, aluminum dichlorohydrate, aluminum sesquichlorohydrate, aluminum chlorohydrex PG, aluminum dichlorohydrex PG, aluminum sesquichlorohydrex PG, aluminum chlorohydrex PEG, aluminum dichlorohydrex PEG, aluminum sesquichlorohydrex PEG, aluminum chloride, aluminum sulfate, aluminum zirconium chlorohydrate, aluminum zirconium trichlorohydrate, aluminum zirconium tetrachlorohydrate, aluminum zirconium pentachlorohydrate, aluminum zirconium octachlorohydrate, aluminum zirconium tetrachlorhydrex propylene glycol, aluminum- zirconium trichlorohydrex Gly, aluminum zirconium tetrachlorohydrex Gly, aluminum zirconium pentachlorohydrex
  • deodorant active examples include, but are not limited to, antimicrobial actives, alcohols, 2,4,4'-trichloro-2'-hydroxy diphenyl ether (Triclosan), benzethonium chloride, potyhexamethytene biguanides, triethylcitrate, 2-amino-2-methyl-1-propanol (AMP), cetyl-trimethylammomium bromide, cetyl pyridinium chloride, farnesol (3,7,11-trimethyl-2,6,10-dodecatrien-1-ol), bactericides, and/or bacteriostats.
  • antimicrobial actives alcohols
  • 2,4,4'-trichloro-2'-hydroxy diphenyl ether Triclosan
  • benzethonium chloride potyhexamethytene biguanides
  • triethylcitrate 2-amino-2-methyl-1-propanol (AMP)
  • AMP 2-amin
  • compositions according to the present invention can include a volatile silicone.
  • volatile silicone is excluded from the composition.
  • the volatile silicone is a volatile cyclic polydimethylsiloxane (cyclomethicone). e.g., cyclopentasiloxane.
  • volatile material it is meant that the material has a measurably vapor pressure at ambient temperature.
  • the volatile cyclic polydimethylsiloxane is cyclomethicone.
  • Various types of cyctomethicones may be used.
  • the volatile silicones are one or more members selected from cyclic polydimethylsiloxanes such as those represented by Formula 1: where n is an integer with a value of 3-7, particularly 5-6.
  • cyclic polydimethylsiloxanes such as those represented by Formula 1: where n is an integer with a value of 3-7, particularly 5-6.
  • suitable cyclomethicones are DC-345 and DC-245, manufactured by Dow Corning Corporation, Midland, MI. These types include a tetramer (octylmethylcyclotetrasiloxane) and a pentamer (decamethylcyclopentasiloxane).
  • the amount of volatile silicone in the composition is greater than 0 up to 40 weight% of the composition. In another embodiment, the amount is less than 40, 35, 30, 25, 20.
  • the composition 15, 10, 5, or 1 weight% of the composition.
  • the combined amount of the plant oil and volatile silicone is up to 50, 45, 40, 35, 30, 25, or 20 weight%.
  • the composition can contain talc. In one embodiment, the amount of talc in the composition is 1 to 10 weight% of the composition.
  • the composition can contain emollients in any desired amount to achieve a desired emollient effect.
  • Emollients are known in the art and are used to impart a soothing effect on the skin.
  • Non-volatile emollients are preferable in the present invention.
  • Classes of non-volatile emollients include non-silicone and silicone emollients.
  • Non-volatile, non-silicone emollients include C 12-15 alkyl benzoate.
  • the non-volatile silicone material can be a polyethersiloxane, polyalkyarylsiloxane or polyethersiloxane copolymer.
  • An illustrative non-volatile silicone material in the present invention is phenyl trimethicone.
  • emollients can be found in United States Patent No. 6,007,799 . Examples include, but are not limited to, PPG-14 butyl ether, PPG-3 myriscyl ether, stearyl alcohol, stearic acid, glyceryl monorieinoleate, isobutyl palmitate, glyceryl monostearate, isocetyl stearate, sulphated tallow, oleyl alcohol, propylene glycol, isopropyl laurate, mink oil, sorbitan stearate, cetyl alcohol, hydrogenated castor oil, stearyl stearate, hydrogenated soy glycerines, isopropyl isostearate, hexyl laurate, dimethyl brassylate, decyl oleate, diisopropyl adipate
  • the composition can additionally include ionizable inorganic salts.
  • M is a member chosen from Na +1 , Li +1 , K +1 , Mg +2 , Ca +2 , Sr +2 , and Zn +2 and
  • X is a member chosen chloride, bromide, iodide, citrate, gluconate, lactate, glycinate, glutamate, ascorbate, aspartate, nitrate, phosphate, hydrogenphosphate, dihydrogenphosphate, formate, maloneate, maleate, succinate, carbonate, bicarbonate, sulfate, and hydrogensulfate.
  • the selected salts are chosen from NaCl and ZnCl 2 .
  • a salt directly to a portion of the mixture during manufacturing, it is desired to add the salt as a mixture or solution of the salt in a carrier or solvent, particularly water.
  • a carrier or solvent particularly water.
  • concentrations of the salt premix can be made.
  • the composition may also contain particulates which include but are not limited to talc, mica, fragrance encapsulates, or hydrophobically modified starches, such as aluminum starch octenyl succinate (MACKADERMTM ASTRO-DRYTM from McIntyre Group Ltd.).
  • particulates include but are not limited to talc, mica, fragrance encapsulates, or hydrophobically modified starches, such as aluminum starch octenyl succinate (MACKADERMTM ASTRO-DRYTM from McIntyre Group Ltd.).
  • the average particle size of the suspended material is sized so that it can pass through the application to prevent the ball applicator from malfunctioning. Usually, the average particle size does not exceed 150 microns.
  • the composition may also contain as an optional ingredient at least one malodor counteracting alpha, beta-unsaturated ester or mixtures of such materials.
  • the level of malodor counteracting composition to deliver a perceivable odor control benefit when deliverer from an antiperspirant and/or deodorant composition is about 0.05 to about 0.45 weight % based on the entire compositions.
  • the alpha, beta-unsaturated ester malodor counteracting materials are incorporated within the oil phase of an antiperspirant composition. Example of these malodor counteracting components can be found in U.S. Patent No. 6,610, 648 and U.S. Patent No. 6,495,097 .
  • the odor neutralizing alpha, beta unsaturated ester mixture demonstrates unexpected stability in antiperspirant compositions containing low metal:chloride (M:Cl) ratio salts free of glycine.
  • M:Cl metal:chloride
  • Examples of the alpha, beta unsaturated ester can be found in WO2005/025523 , which was filed in the United States as U.S. Application No. 10/571,488 .
  • alpha, beta unsaturated ester examples include, but are not limited to,:
  • the composition may optionally further comprise absorbent materials such as corn starch, talc, clay, sodium polyacrylate and/or cotton fiber; and/or other materials such as fragrances, bacteriostats and/or bacteriosides, colorants, etc.
  • absorbent materials such as corn starch, talc, clay, sodium polyacrylate and/or cotton fiber
  • other materials such as fragrances, bacteriostats and/or bacteriosides, colorants, etc.
  • bacteriostats include baceteriostatic quaternary ammonium compounds such as 2-amino-2-methyl-1-propanol (AMP), cetyl-trimethylammomium bromide, cetyl pyridinium chloride, 2,4,4N-trichloro-2N-hydroxydiphenylether (Triclosan), etc. and various zinc salts.
  • AMP 2-amino-2-methyl-1-propanol
  • Triclosan 2,4,4N-trichloro-2N-hydroxydiphenylether
  • Antioxidants may be added to the composition, preferably to act as ingredient protectants and for maintenance of long-term stability of the composition.
  • Suitable antioxidants include Tinogard, manufactured by Ciba Specialty Chemicals, Basel, Switzerland.
  • compositions as provided herein are described and claimed with reference to their ingredients, as is usual in the art. As would be evident to one skilled in the art, ingredients may in some instances react with one another, so that the true composition of the final formulation may not correspond exactly to the ingredients listed. Thus, it should be understood that the invention extends to the product of the combination of the listed ingredients.
  • compositions of the present invention may be manufactured using methods known in the art. Typically, the ingredients are combined and heated to melt the components (other than inert filler), and the melted components (together with particulate inert filler) are mixed. Desirably, volatile materials, such as the fragrance materials, are incorporated in the composition in the latter stages of the mixing cycle, in order to avoid volatilization thereof. After mixing, the molten composition can be poured directly into the dispensers, after which the compositions harden into a solid, and the container is capped to preserve the product until use.
  • volatile materials such as the fragrance materials
  • the composition is a solid stick when at ambient room temperature of about 25°C.
  • the stick form is an example of a solid form.
  • the stick form can be distinguished from a soft solid in that, in a stick, the formulated product can retain its shape for extended time periods outside the package, the product not loosing its shape significantly (allowing for some shrinkage due to solvent evaporation). Adjustment of amounts of gelling or thickening agents can be used in order to form a stick.
  • the composition is an anhydrous stick.
  • anhydrous it is meant that no separate water is added but there could be moisture associated with materials that are added to the composition.
  • the amount of water is zero or less than 3, 2, 1, 0.5, or 0.1 weight % of the composition.
  • the compression force of the composition is at least 3500g. In other embodiments, the compression force is at least 4000g, at least 4500g, at least about 5000g, at least 6000g, at least 7000g, at least about 8000g, at least 9000g. In another embodiment, the compression force is 3500g to 10,000g.
  • the composition can provide a payout of about 0.7 to about 0.9g according to the payout test on the Payout, Glide, and Flakeoff Test Machine, which is the machine and method described in WO2009/045557 .
  • the composition can provide a glide of about 0.8 to about 1.4g according to the glide test on the Payout, Glide, and Flakeoff Test Machine.
  • the composition can provide a flakeoff of less that about 25%. In other embodiments, the flake off is less than about 20, about 15, about 10, or about 5%. In other embodiments, the amount of flakeoff is about 1 to about 6%.
  • Compression strength of a stick product is measured using a Texture Analyzer Model # TA-ZT21 from Texture Technologies.
  • the compression probe is a 19 mm square end probe.
  • a 42.5 g (1.5 oz) antiperspirant stick is selected.
  • the antiperspirant stick is removed from the barrel and placed in a hardness sample holder.
  • the stick is positioned such that 2.54cm (1 inch) of the sample, measured at the edge of the domed portion, is exposed for the test.
  • the cover on the hardness holder is closed and the holder positioned so that the blade comes in contact with the midpoint of the exposed sample.
  • the instrument is set to the following parameters:
  • the stick compositions bellow are made by standard methods of melting the materials and mixing them together.
  • the comparative examples are typical antiperspirant stick compositions.
  • the Examples use the high levels of fatty acid in combination with plant oil.
  • the stick compositions below are made by standard methods of melting the materials and mixing them together.
  • the compositions below contain talc.
  • Material Comparative 3 4 5 Cyclomethicone 35 30 30
  • Stearyl Alcohol 16 0 0 C12-15 Alkyl Benzoate 10 0 0 PPG-14 Butyl Ether 6 0 0 Castor Wax (80°C melt point) 5
  • Hydrogenated Soybean Oil iodine value up to 20 2 2 2 PEG-8 Distearate 3 3 3 3 3 3 3
  • Talc 2 2
  • Palm Kernel Oil 0 0 21 Palmitic Acid 0 16 16 Fragrance 1

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
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EP09793162.0A 2009-09-30 2009-09-30 Antiperspirant composition Active EP2482795B1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US2009/058957 WO2011040909A1 (en) 2009-09-30 2009-09-30 Antiperspirant/deodorant composition

Publications (2)

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EP2482795A1 EP2482795A1 (en) 2012-08-08
EP2482795B1 true EP2482795B1 (en) 2016-05-04

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US (1) US20110076310A1 (es)
EP (1) EP2482795B1 (es)
AR (1) AR078194A1 (es)
AU (1) AU2009353310B2 (es)
BR (1) BR112012006851B1 (es)
CA (1) CA2773164C (es)
ES (1) ES2585741T3 (es)
MX (1) MX344017B (es)
RU (1) RU2523898C2 (es)
WO (1) WO2011040909A1 (es)
ZA (1) ZA201202222B (es)

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EP3644951A1 (en) 2017-06-30 2020-05-06 The Procter and Gamble Company Hair care compositions comprising a 2-pyridinol-n-oxide material and an iron chelator
US10905647B2 (en) 2017-06-30 2021-02-02 The Procter & Gamble Company Antiperspirant and deodorant compositions
US10543164B2 (en) 2017-06-30 2020-01-28 The Procter & Gamble Company Deodorant compositions
CN111386101B (zh) * 2017-11-30 2023-10-13 高露洁-棕榄公司 口腔护理组合物
CA3091381A1 (en) * 2018-03-23 2019-09-26 The Procter & Gamble Company Deodorants and antiperspirants comprising a liquid triglyceride, natural fragrances, and piroctone olamine

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AR078194A1 (es) 2011-10-19
MX2012003030A (es) 2012-04-19
CA2773164C (en) 2014-09-16
AU2009353310A1 (en) 2012-03-22
MX344017B (es) 2016-12-02
CA2773164A1 (en) 2011-04-07
RU2012117823A (ru) 2013-11-10
RU2523898C2 (ru) 2014-07-27
WO2011040909A1 (en) 2011-04-07
ZA201202222B (en) 2014-09-25
BR112012006851A2 (pt) 2020-08-18
BR112012006851B1 (pt) 2021-03-09
US20110076310A1 (en) 2011-03-31
EP2482795A1 (en) 2012-08-08
AU2009353310B2 (en) 2013-03-28

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